158478-70-7

Basic information

• Product Name: N,N′-di-tert-butoxycarbonyl-N″-(cyclohexyl)guanidine
• Synonyms: N,N′-di-tert-butoxycarbonyl-N″-(cyclohexyl)guanidine
• CAS NO: 158478-70-7
• Molecular Weight: 341.451
• Mol File: 158478-70-7.mol

Chemical Properties

• CAS DataBase Reference: N,N′-di-tert-butoxycarbonyl-N″-(cyclohexyl)guanidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N′-di-tert-butoxycarbonyl-N″-(cyclohexyl)guanidine(158478-70-7)
• EPA Substance Registry System: N,N′-di-tert-butoxycarbonyl-N″-(cyclohexyl)guanidine(158478-70-7)

Safety Data

• Hazardous Substances Data: 158478-70-7(Hazardous Substances Data)

Upstream product

• 108-91-8 cyclohexylamine 
• 152120-54-2 N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine 
• 216584-22-4 N¹,N²,N³-tris(tert-butoxycarbonyl)guanidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 332882-82-3 1,3-bis(t-butoxycarbonyl)guanidine 
• 145013-05-4 tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate 
• 322474-21-5 N,N'-bis-Boc-S-methyl-isothiourea 
• 207857-15-6 1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine 

Downstream Products

• 14948-83-5 N-cyclohexylquanidine 
• 2498-47-7 N-cyclohexylguanidine hydrochloride 

Relevant articles and documents

Iodine-catalyzed guanylation of amines with N, N ′-di-Boc-thiourea

Herein, we report that iodine-catalyzed guanylation of primary amines can be accomplished with N,N′-di-Boc-thiourea and TBHP to afford the corresponding guanidines in 40-99% yields. Oxidation of the HI byproduct by TBHP eliminates the need for an extra base to prevent the protonation of substrates and makes the reaction especially useful for both electronically and sterically deactivated primary anilines.

Method for synthesizing substituted guanidine

The invention provides a method for synthesizing substituted guanidine. The method of the invention is provided against heavy metals or complex oxidants needed in convectional methods for synthesizingthe substituted guanidine. The method comprises the following steps: carrying out an elemental iodine-mediated thiourea desulphurization reaction on economical and easily available N,N'-bis-tert-butoxycarbonylthiourea to generate an active carbodiimide active intermediate, and attacking the intermediate with free amine to remove a protecting group in order to finally realize the preparation of the guanidine containing different substituent groups. The method for synthesizing substituted guanidine of the present invention has the advantages of mild reaction conditions and high efficiency, andis expected to be applied to later modification of drug molecules and natural products.

Synthetic method for preparing substituted guanidine by iodine-catalyzed thiourea desulfurization

The invention discloses a synthetic method for preparing substituted guanidine by iodine-catalyzed thiourea desulfurization, aiming at the fact that excessive heavy metals or oxidizing agents are required for synthesizing substituted guanidine in a traditional method. According to the method, starting from economical N,N'-di-tert-butyloxycarbonyl thiourea easy to obtain, a catalyst-involved thiourea desulfurization reaction is carried out to realize the preparation of guanidine containing different substituents. The synthetic method for preparing the substituted guanidine does not need additional alkali, has high atom economy and is mainly used for late modification of drug molecules and natural products.

Synthesis of guanidines via the I2 mediated desulfurization of N,N′-di-Boc-thiourea

The I2 mediated desulfurization of N,N′-di-Boc-thiourea was developed. Various primary amines, including sterically and electronically deactivated primary amines, were transformed into the corresponding bis-Boc protected guanidines under mild conditions.

ANTIMICROBIAL GUANIDINIUM AND THIOURONIUM FUNCTIONALIZED POLYMERS

Antimicrobial cationic polycarbonates and polyurethanes have been prepared comprising one or more pendent guanidinium and/or isothiouronium groups. Additionally, antimicrobial particles were prepared having a silica core linked to surface groups comprising a guanidinium and/or isothiouronium group. The cationic polymers and cationic particles can be potent antimicrobial agents against Gram-negative microbes, Gram-positive microbes, and/or fungi.

NIS-promoted guanylation of amines

An efficient NIS-promoted guanylation reaction is described. This procedure allows the guanylation of primary and secondary amines through the reaction with di-Boc-thiourea and di-Boc-S-methylisothiourea, respectively. We demonstrated that the use of NIS compares favorably with existing methods and is an attractive alternative to heavy metal or Mukayama's reagent activation.

N,N′,N″-Tri-Boc-guanidine (TBG): a common starting material for both N-alkyl guanidines and amidinoureas

In this Letter, we describe the unexpected reaction pattern of N,N′N″-tri-Boc-guanidine (TBG) with amines at room temperature and under reflux conditions affording N-substituted guanidines and amidinoureas, potentially important compounds with extensive a

A novel, facile methodology for the synthesis of N,N′-bis(tert-butoxycarbonyl)-protected guanidines using polymer-supported carbodiimide

A novel methodology for the synthesis of guanidines from amines has been developed using polymer assisted synthesis, potentially allowing the preparation of series of compounds in a high throughput manner. The methodology comprises the use of polymer-supported carbodiimide as the activating agent for N,N′-bis(tert-butoxycarbonyl) thiourea with polymer-supported trisamine as a scavenger, followed by deprotection with trifluoroacetic acid. For the first time, polymer-supported carbodiimide has been utilized as an activating agent to synthesize guanidines.

Conversion of N,N'-bis(tert-butoxycarbonyl)guanidines to N-(N'-tert-butoxycarbonylamidino)ureas

Surprising aminolysis of bis-Boc-protected guanidines in refluxing THF leads to the corresponding monoBoc substituted amidinoureas.